Cleavage of alpha-oximinoketones, aldehydes and acetals and their nitroso isomers

ABSTRACT

The cleavage forms an ester group and a cyano group. It is effected by use of an ortho ester of a carboxylic acid, or reaction product thereof with the oximino compound or with a Lewis acid such as boron trifluoride in an electrophilic reaction medium. In particular alpha-oximinocyclohexanone dimethyl acetal is cleaved to form omega-cyano methyl valerate by catalytic action of dimethoxy ethylcarbonium tetrafluoroborate in dichloromethane solvent. The cyclic C5, C8, and C12 homologues react similarly; likewise the alkyl-substituted homologues and the nitroso isomers.



